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2099 HELMSLEY AVENUE
1019 - WM Westmount Oakville (WM Westmount) L6M 4R5

$2,450,000
Single Family beds: 5 baths: 4.0

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Photo 1: 2099 HELMSLEY AVENUE in Oakville (WM Westmount): Single Family for sale : MLS®# W12810144
Photo 2: 2099 HELMSLEY AVENUE in Oakville (WM Westmount): Single Family for sale : MLS®# W12810144
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Photo 20: 2099 HELMSLEY AVENUE in Oakville (WM Westmount): Single Family for sale : MLS®# W12810144
Photo 21: 2099 HELMSLEY AVENUE in Oakville (WM Westmount): Single Family for sale : MLS®# W12810144
Photo 22: 2099 HELMSLEY AVENUE in Oakville (WM Westmount): Single Family for sale : MLS®# W12810144
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Photo 42: 2099 HELMSLEY AVENUE in Oakville (WM Westmount): Single Family for sale : MLS®# W12810144
Photo 43: 2099 HELMSLEY AVENUE in Oakville (WM Westmount): Single Family for sale : MLS®# W12810144
Photo 44: 2099 HELMSLEY AVENUE in Oakville (WM Westmount): Single Family for sale : MLS®# W12810144
Photo 45: 2099 HELMSLEY AVENUE in Oakville (WM Westmount): Single Family for sale : MLS®# W12810144
Photo 46: 2099 HELMSLEY AVENUE in Oakville (WM Westmount): Single Family for sale : MLS®# W12810144
Photo 47: 2099 HELMSLEY AVENUE in Oakville (WM Westmount): Single Family for sale : MLS®# W12810144
Status:
Active
Prop. Type:
Single Family
MLS® Num:
W12810144
Bedrooms:
5
Bathrooms:
4
Your Private Summer Oasis in Westmount! Stop scrolling! 2099 Helmsley Ave has officially hit the market, and it's the definition of "turn-key." This isn't just a house; it's a 3,300+ sq. ft. lifestyle upgrade in one of Oakville's most coveted pockets. Why you'll fall in love: Fully Renovated: Brand-new kitchen and spa-like baths. No carpet on the main or upper floors-just sleek, clean lines. Room for Everyone: 4+1 Bedrooms plus a separate office on the main floor, 4 Baths, and a massive finished basement for gym/office/play. The Backyard (The Real MVP): A massive, sun-drenched lot with an in-ground pool, gazebo, and still tons of grass for the kids/pups to run. It is the spot for summer 2026. Meticulously Maintained: Extended driveway and oversized rooms that actually fit your furniture. The Neighborhood Perks: Top-ranked schools (Captain R. Wilson & Garth Webb) Minutes to the Oakville Trafalgar Memorial Hospital, Shops, Oakville Transit, and easy Hwy 407/QEW access are right around the corner. (id:2493)
Property Type:
Single Family
Common Interest:
Freehold
Property Attached:
No
Living Area (Min):
3,000 sq. ft.
Living Area (Max):
3,500 sq. ft.
Zoning:
RL6
Taxes:
$9,782 / 2025
Community:
1019 - WM Westmount
Features:
Fireplace(s)
Exterior Features:
Brick
Pool Features:
Inground pool
Structure Type:
House
Utilities:
Sewer, Electricity, Cable
Appliances Included:
Washer, Refrigerator, Water meter, Dishwasher, Stove, Dryer, Microwave, Window Coverings, Garage door opener remote(s)
Bedrooms:
5
Bedrooms Above Grade:
4
Bedrooms Below Grade:
1
Bathrooms:
4.0
Half Bathrooms:
1
Cooling:
Central air conditioning
Fireplace:
Yes
Fireplaces:
1
Foundation:
Poured Concrete
Heating:
Forced air, Natural gas
# Storeys:
2.0
Water:
Municipal water
Sewer:
Sanitary sewer
Basement:
Finished, N/A
Fence Type:
Fenced yard
Lot Frontage:
35'4"
Lot Details:
35.3 x 140.4 FT ; Large Pie Lot
Lot Features:
Flat site, Gazebo
Parking:
Garage
Total Parking Spaces:
5
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    front
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    Entry hall
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    Entry Hall
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    stairs
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    family
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    family
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    family
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    kitchen
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    kitchen
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    main floor laundry
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    dining
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    living
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    office
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    master
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    master
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    master
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    master
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    ensuite
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    master ensuite
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    Bed2
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    Bed 3
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    family Bath
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    Bed 4
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    Basement bath
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    recroom
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    Basement Bedroom
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Listed by Century 21 Miller Real Estate Ltd.
Data was last updated February 23, 2026 at 12:15 AM (UTC)
Area Statistics
Listings on market:
60
Avg list price:
$612,000
Min list price:
$439,000
Max list price:
$2,179,800
Avg days on market:
31
Min days on market:
1
Max days on market:
198
Avg price per sq.ft.:
$643.36
These statistics are generated based on the current listing's property type and located in 1019 - WM Westmount. Average values are derived using median calculations. This data is not produced by the MLS® system.
The trademarks REALTOR®, REALTORS®, and the REALTOR® logo are controlled by The Canadian Real Estate Association (CREA) and identify real estate professionals who are member’s of CREA. The trademarks MLS®, Multiple Listing Service® and the associated logos are owned by CREA and identify the quality of services provided by real estate professionals who are members of CREA. Used under license.